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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:12 UTC
Update Date2021-09-14 15:45:15 UTC
HMDB IDHMDB0061007
Secondary Accession Numbers
  • HMDB61007
Metabolite Identification
Common NameN-Desmethyltramadol
DescriptionN-Desmethyltramadol, also known as M2, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. N-Desmethyltramadol is a very strong basic compound (based on its pKa). N-Desmethyltramadol is a metabolite of tramadol. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. Within humans, N-desmethyltramadol participates in a number of enzymatic reactions. In particular, N-desmethyltramadol and formaldehyde can be biosynthesized from tramadol through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In addition, N-desmethyltramadol can be converted into N,N-didesmethyltramadol and formaldehyde through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In humans, N-desmethyltramadol is involved in tramadol metabolism pathway. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia ).
Structure
Data?1563866133
Synonyms
ValueSource
N-DemethyltramadolHMDB
N-MonodesmethyltramadolHMDB
M2HMDB
Chemical FormulaC15H23NO2
Average Molecular Weight249.354
Monoisotopic Molecular Weight249.172878985
IUPAC Name(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol
Traditional Name(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol
CAS Registry Number75377-45-6
SMILES
CNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C1
InChI Identifier
InChI=1S/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1
InChI KeyVUMQHLSPUAFKKK-HIFRSBDPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Cyclohexanol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.55ALOGPS
logP2.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)9.89ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.97 m³·mol⁻¹ChemAxon
Polarizability28.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+162.54530932474
DeepCCS[M-H]-160.18730932474
DeepCCS[M-2H]-193.07330932474
DeepCCS[M+Na]+168.63830932474
AllCCS[M+H]+159.832859911
AllCCS[M+H-H2O]+156.032859911
AllCCS[M+NH4]+163.332859911
AllCCS[M+Na]+164.332859911
AllCCS[M-H]-164.832859911
AllCCS[M+Na-2H]-165.232859911
AllCCS[M+HCOO]-165.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-DesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C12489.2Standard polar33892256
N-DesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C12004.0Standard non polar33892256
N-DesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C12003.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desmethyltramadol,1TMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(OC)=C12018.9Semi standard non polar33892256
N-Desmethyltramadol,1TMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C12135.7Semi standard non polar33892256
N-Desmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C12094.8Semi standard non polar33892256
N-Desmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C12229.5Standard non polar33892256
N-Desmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C12506.1Standard polar33892256
N-Desmethyltramadol,1TBDMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC)=C12234.7Semi standard non polar33892256
N-Desmethyltramadol,1TBDMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C12374.4Semi standard non polar33892256
N-Desmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C12582.5Semi standard non polar33892256
N-Desmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C12693.7Standard non polar33892256
N-Desmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C12721.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyltramadol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Positive-QTOFsplash10-0ue9-0090000000-9d8c3a60e2de49d18cbe2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Positive-QTOFsplash10-0udi-2190000000-c10e96139d56f74ccd892019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Positive-QTOFsplash10-0pvl-9110000000-15b8680c6f67759db4632019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Negative-QTOFsplash10-0002-0090000000-a5467e9c52e23f3b2cae2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Negative-QTOFsplash10-06rt-2590000000-2ad5f4ba239587708ca22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Negative-QTOFsplash10-001l-7950000000-df5a085772b193c930912019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Positive-QTOFsplash10-0uxr-0090000000-b61eecfd3959c0eb9cd92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Positive-QTOFsplash10-0f6x-4590000000-44a7a4306129ff2442002021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Positive-QTOFsplash10-0udi-6690000000-dc8d206de089d73f9d832021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Negative-QTOFsplash10-0002-0090000000-a9ac8288dd5151a7660e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Negative-QTOFsplash10-0002-0290000000-75a0f9a4cea95a26ce312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Negative-QTOFsplash10-000l-1910000000-3ffeb2cf3582eadafc7b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23935864
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmetramadol
METLIN IDNot Available
PubChem Compound12149038
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available